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CA2046949A1 - Process for preparing perfluoroalkoxysulphonic compounds - Google Patents

Process for preparing perfluoroalkoxysulphonic compounds

Info

Publication number
CA2046949A1
CA2046949A1 CA002046949A CA2046949A CA2046949A1 CA 2046949 A1 CA2046949 A1 CA 2046949A1 CA 002046949 A CA002046949 A CA 002046949A CA 2046949 A CA2046949 A CA 2046949A CA 2046949 A1 CA2046949 A1 CA 2046949A1
Authority
CA
Canada
Prior art keywords
formula
compounds
perfluoroalkoxysulphonic
preparing
iii
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CA002046949A
Other languages
French (fr)
Other versions
CA2046949C (en
Inventor
Walter Navarrini
Vittorio Montanari
Anna Maria Staccione
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Solvay Specialty Polymers Italy SpA
Original Assignee
Individual
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Individual filed Critical Individual
Publication of CA2046949A1 publication Critical patent/CA2046949A1/en
Application granted granted Critical
Publication of CA2046949C publication Critical patent/CA2046949C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0215—Sulfur-containing compounds
    • B01J31/0225—Sulfur-containing compounds comprising sulfonic acid groups or the corresponding salts
    • B01J31/0227—Sulfur-containing compounds comprising sulfonic acid groups or the corresponding salts being perfluorinated, i.e. comprising at least one perfluorinated moiety as substructure in case of polyfunctional compounds
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D19/00—Degasification of liquids
    • B01D19/02—Foam dispersion or prevention
    • B01D19/04—Foam dispersion or prevention by addition of chemical substances
    • B01D19/0404—Foam dispersion or prevention by addition of chemical substances characterised by the nature of the chemical substance
    • B01D19/0427—Foam dispersion or prevention by addition of chemical substances characterised by the nature of the chemical substance compounds containing halogen-atoms
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0215—Sulfur-containing compounds
    • B01J31/0222—Sulfur-containing compounds comprising sulfonyl groups
    • B01J31/0224—Sulfur-containing compounds comprising sulfonyl groups being perfluorinated, i.e. comprising at least one perfluorinated moiety as substructure in case of polyfunctional compounds
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0215—Sulfur-containing compounds
    • B01J31/0225—Sulfur-containing compounds comprising sulfonic acid groups or the corresponding salts
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0231—Halogen-containing compounds
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
    • B01J31/0235—Nitrogen containing compounds
    • B01J31/0237—Amines
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
    • B01J31/0271—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds also containing elements or functional groups covered by B01J31/0201 - B01J31/0231
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
    • C07C303/22—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof from sulfonic acids, by reactions not involving the formation of sulfo or halosulfonyl groups; from sulfonic halides by reactions not involving the formation of halosulfonyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01—Sulfonic acids
    • C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
    • C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C309/07—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing oxygen atoms bound to the carbon skeleton
    • C07C309/09—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing oxygen atoms bound to the carbon skeleton containing etherified hydroxy groups bound to the carbon skeleton
    • C07C309/10—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing oxygen atoms bound to the carbon skeleton containing etherified hydroxy groups bound to the carbon skeleton with the oxygen atom of at least one of the etherified hydroxy groups further bound to an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/78—Halides of sulfonic acids
    • C07C309/79—Halides of sulfonic acids having halosulfonyl groups bound to acyclic carbon atoms
    • C07C309/82—Halides of sulfonic acids having halosulfonyl groups bound to acyclic carbon atoms of a carbon skeleton substituted by singly-bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/22—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms
    • C07C311/23—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atoms of the sulfonamide groups bound to acyclic carbon atoms
    • C07C311/24—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atoms of the sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/004—Surface-active compounds containing F
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M6/00—Primary cells; Manufacture thereof
    • H01M6/14—Cells with non-aqueous electrolyte
    • H01M6/16—Cells with non-aqueous electrolyte with organic electrolyte
    • H01M6/162—Cells with non-aqueous electrolyte with organic electrolyte characterised by the electrolyte
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
    • B01J2231/42—Catalytic cross-coupling, i.e. connection of previously not connected C-atoms or C- and X-atoms without rearrangement
    • B01J2231/4205—C-C cross-coupling, e.g. metal catalyzed or Friedel-Crafts type
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M6/00—Primary cells; Manufacture thereof
    • H01M6/14—Cells with non-aqueous electrolyte
    • H01M6/16—Cells with non-aqueous electrolyte with organic electrolyte
    • H01M6/162—Cells with non-aqueous electrolyte with organic electrolyte characterised by the electrolyte
    • H01M6/168—Cells with non-aqueous electrolyte with organic electrolyte characterised by the electrolyte by additives

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Manufacturing & Machinery (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Electrochemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Toxicology (AREA)
  • Dispersion Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

A process for preparing perfluoroalkoxysulphonic compounds having formula:
R f ~ OC2F4 -SO2X)p (I) wherein R f represents a perfluoroalkyl or perfluoroethereal group, X represents F, OH or OM, in which M is an alkaline cation, alkaline-earth cation, or X represents NR1R2, in which R1 and R2, independently of each other, represent H or an alkyl group containing from 1 to 5 carbon atom and p is a number selected from 1 to 2, characterized in that the perfluoro vinyl sulphonyl fluoride of formula (II) CF2 = CF-SO2F is reacted with a hypofluorite of formula (III):
R f (OF) r (III) wherein R f is the same as defined above, and r represents 1 or 2, optionally in an inert solvent, at a temperature approximately ranging from -140°C to +40°C, and that, if so desired, from the compound of formula (I) so obtained in which X=F, the corresponding derivatives, in which X has the other meanings defined above, are obtained by means of conventional techniques. A few subclasses of compounds (I) are new per se.
The derivatives are utilized as polymerization catalysts, surfactants, electrolytes in electric generators.
CA002046949A 1990-07-12 1991-07-12 Process for preparing perfluoroalkoxysulphonic compounds Expired - Fee Related CA2046949C (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IT20920A/90 1990-07-12
IT02092090A IT1246357B (en) 1990-07-12 1990-07-12 PROCESS FOR THE PREPARATION OF PERFLUOROALCOXYSULPHONIC COMPOUNDS

Publications (2)

Publication Number Publication Date
CA2046949A1 true CA2046949A1 (en) 1992-01-13
CA2046949C CA2046949C (en) 2002-12-10

Family

ID=11174094

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002046949A Expired - Fee Related CA2046949C (en) 1990-07-12 1991-07-12 Process for preparing perfluoroalkoxysulphonic compounds

Country Status (6)

Country Link
US (2) US5241110A (en)
EP (1) EP0466483B1 (en)
JP (1) JP3167356B2 (en)
CA (1) CA2046949C (en)
DE (1) DE69113695T2 (en)
IT (1) IT1246357B (en)

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* Cited by examiner, † Cited by third party
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FR2704099B1 (en) * 1993-04-15 1995-07-07 Centre Nat Etd Spatiales ELECTROLYTE FOR ELECTRIC BATTERY.
US5358801A (en) * 1993-09-03 1994-10-25 Valence Technology, Inc. Solid electochemical cell of improved capacity and cycling capability having surfactant in vanadium oxide cathode mixture
FR2717620A1 (en) * 1994-03-21 1995-09-22 Centre Nat Rech Scient Additive limiting the corrosion of the collector in an electrochemical cell.
EP0699349B1 (en) * 1994-03-21 2007-10-10 Centre National De La Recherche Scientifique (Cnrs) Ionic conducting material having good anticorrosive properties
RU2125555C1 (en) * 1995-02-08 1999-01-27 Хальдор Топсеэ А/С Process for preparing fluorinated sulphonic acid
CA2704986C (en) * 1996-12-30 2013-04-09 Hydro-Quebec Use of an ionic compound, derived from malononitrile as a photoinitiator, radical initiators or catalyser in polymerization processes or as a basic dye
WO1999030381A1 (en) * 1997-12-10 1999-06-17 Minnesota Mining And Manufacturing Company Bis(perfluoroalkylsulfonyl)imide surfactant salts in electrochemical systems
IT1313597B1 (en) * 1999-08-04 2002-09-09 Ausimont Spa FLUOROPOLYEREOUS LUBRICANTS CONTAINING SULPHONYLFLUORIDE GROUPS
JP2001114750A (en) * 1999-10-19 2001-04-24 Daikin Ind Ltd Method for producing perfluorovinyl ether sulfonic acid derivative
ITMI20012744A1 (en) * 2001-12-21 2003-06-21 Ausimont Spa POLYMERIZATION PROCESS OF SULPHONIC MONOMERS
ITMI20020198A1 (en) 2002-02-05 2003-08-05 Ausimont Spa (PER) haloethers
US6624328B1 (en) * 2002-12-17 2003-09-23 3M Innovative Properties Company Preparation of perfluorinated vinyl ethers having a sulfonyl fluoride end-group
US7348088B2 (en) * 2002-12-19 2008-03-25 3M Innovative Properties Company Polymer electrolyte membrane
JP5558067B2 (en) * 2008-10-15 2014-07-23 三菱マテリアル株式会社 Method for producing perfluorosulfonic acid having an ether structure and derivatives thereof, and surfactant containing fluorine-containing ether sulfonic acid compound and derivatives thereof
JP2010095470A (en) * 2008-10-16 2010-04-30 Asahi Glass Co Ltd Method for producing fluorine-containing compound having fluorosulfonyl group
US7977426B2 (en) * 2008-11-13 2011-07-12 E. I. Du Pont De Nemours And Company Fluoroalkyl ether sulfonate surfactants
KR101431926B1 (en) * 2009-09-29 2014-08-19 미쓰비시 마테리알 가부시키가이샤 Method for producing perfluorosulfonic acid having ether structure and derivative thereof, and surfactant containing fluorine-containing ether sulfonic acid compound and derivative thereof
US10246572B2 (en) 2010-12-16 2019-04-02 Solvay Specialty Polymers Italy S.P.A. Foamable fluoropolymer compositions
EP2785781A1 (en) 2011-11-28 2014-10-08 Solvay Specialty Polymers USA, LLC. Polymer composition
DE102012101670A1 (en) * 2012-02-29 2013-08-29 Jacobs University Bremen Ggmbh Conducting salt for lithium-based energy storage

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US3560568A (en) 1968-11-26 1971-02-02 Du Pont Preparation of sulfonic acid containing fluorocarbon vinyl ethers
US3821290A (en) 1971-03-01 1974-06-28 Allied Chem Polyfluoroisoalkoxyalkyl sulfonic acids
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DE3043427A1 (en) * 1980-11-18 1982-07-08 Bayer Ag, 5090 Leverkusen PERFLUORED SULPHONIC ACID FLUORIDES AND METHOD FOR THE PRODUCTION THEREOF
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Also Published As

Publication number Publication date
IT1246357B (en) 1994-11-17
JP3167356B2 (en) 2001-05-21
EP0466483B1 (en) 1995-10-11
CA2046949C (en) 2002-12-10
DE69113695D1 (en) 1995-11-16
IT9020920A0 (en) 1990-07-12
JPH06128216A (en) 1994-05-10
IT9020920A1 (en) 1992-01-12
US5374770A (en) 1994-12-20
DE69113695T2 (en) 1996-05-15
US5241110A (en) 1993-08-31
EP0466483A1 (en) 1992-01-15

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Effective date: 20090713